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1* "Little Susie" from ''Music/HistoryPastPresentAndFutureBookI''. Made more poignant by the singing of a small girl at the beginning.
2* "Heal The World" from ''Music/{{Dangerous|Album}}''. It's sadder now that he's gone.
3* "Gone Too Soon", also from ''Dangerous'', is a song written for Ryan White, an AIDS victim (due to a tainted blood transfusion) who was also one of the earliest advocates for research and acceptance of those afflicted with it. He and Jackson were friends for a while. MTV played it after Jackson himself died. And people all over wept.
4* "You Are Not Alone" and "Earth Song" from ''Music/HistoryPastPresentAndFutureBookI'', "Man In The Mirror" from ''Music/{{Bad}}'', "Will You Be There" from ''Music/{{Dangerous|Album}}'' and "Cry" from ''Music/{{Invincible}}''. Made EVEN sadder when these songs (along with the aforementioned two) were played right after he was pronounced dead. "You Are Not Alone" is especially sad because it seems like he is singing it to himself.
5* Then there are "She's Out of my Life", from ''Music/OffTheWall''. He even breaks down crying near the end.
6* The music video of ''Earth Song'', with all the images of slaughtered animals, pollution, war crimes, and the general air of the worst of humanity on full display.
7** In ''This Is It'', the video for ''"Earth Song"'' has a little girl in a rainforest who seemingly dies trying to save a single flower from a bulldozer. In an interview with the actress who portrayed the little girl, she mentions that in the actual concerts she was supposed to emerge to the stage, with the plant, alive.
8** The song becomes more relevant in 21st century due to UsefulNotes/TheWarOnTerror and global warming.
9* Once again, the song, "Childhood" from ''Music/HistoryPastPresentAndFutureBookI''.
10** The lyrics "Have you seen my childhood?" Takes on a tragic double meaning in that of "Did you know about '''''my''''' childhood?" and "Where was the childhood I never got to have."
11** Michael himself sounds like he's in tears by the end of the song.
12* "Smile", also from ''Music/HistoryPastPresentAndFutureBookI''. While the song is supposed to be a cover of a Charlie Chaplin song with the same name, the way how the background music sounds and the way how Michael sings the lyrics makes it more melancholy than uplifting. In the final portion of the song, during the bittersweet piano passage, Michael is heard whistling the notes. After it finishes, he can be heard crying softly.
13* The music video for "Who Is It". Michael believes that his lover is cheating on him, having found a business card with the name "Alex" printed on it. Turns out that she's a high class prostitute who has her appearance changed for each client and that the card Michael found is hers, one of her many aliases. Towards the end, she escapes from her handlers and flees to Michael's house but it's too late, he has already left and when she begs to be let in Michael's employee just drops a handful of her name cards at her feet showing her that she's been found out. She's forced to return to her handlers, one slapping her for running off, before being having her makeup cleaned off so she can get back to work.
14* Also, "Ben". How much of a tearjerker this is may vary depending on whether or not you're aware that Ben is a ''rat''. Not a scummy guy, a ''literal'' rat.
15** It is given even more poignant meaning after it was covered by Marti Webb as a tribute to Ben Hardwick, an infant who won a televised bid for a liver transplant, only to tragically pass away only a year after.
16* "Is It Scary". Especially for people who get made fun of because of their appearance.
17** To a lesser extent, "Threatened" from ''Music/{{Invincible}}''.
18* The breakdown of "Morphine," from ''Blood on the Dance Floor: [=HIStory=] in the Mix'' where the IndustrialMetal drums suddenly cut off and are replaced with an orchestra, while Jackson comes as close as he ever could to outright confessing his addiction to painkillers. Because it was on one of his later, less-acclaimed albums, no one really noticed it until his later work was being re-evaluated after his death... from an overdose on painkillers.
19* The poem at the end of "Will You Be There". Even more so, after Michael Jackson's 2009 death, implying that it really was a cry for help.
20* "Stranger in Moscow" from ''Music/{{HIStory|PastPresentAndFutureBookI}}''. [[TheWoobie He's really alone...]]
21* The song "Someone in the Dark" from the ''Film/ETTheExtraTerrestrial Storybook Album''. Not only does the song sound bittersweet but it's sadder when one remembers his passing, especially the line [[HarsherInHindsight "Oh I believe you and I could never really say goodbye."]]
22* The song "Be Not Always" from the Music/TheJacksonFive album ''Music/{{Victory}}''.
23* "Best of Joy" could be considered one as well, from the posthumous album "Michael." While the track itself is lighthearted enough, it was, according to "Man in the Music," one of the last songs he ever recorded. [[https://youtu.be/WOdZy0mO9Vs?t=2m27s The end where his voice fades away over repeated choruses of "I am forever"]] brings a tear to the eye.
24* "[[https://www.youtube.com/watch?v=QNJL6nfu__Q They Don't Care About Us,]]" The song itself is sad with its message of being ignored and uncared about by the government, but especially so tied with the music video in Brazil considering how true it is.
25** The [[https://www.youtube.com/watch?v=PoEa9bzeTu0 2020 version]] is sad for the fact a song released in ''1995'' is still so relevant today and the video itself adds in footage of the worldwide Black Lives Matter protests that had occured that year just hammers that point home.

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